Organic Chemistry Help Line

[UWBodybuilding]

Bane agreed to help me with some O-chem problems I've been having. That was in a thread in the review section, so I moved it to the misc. Anyone else with o-chem problems or solutions, please chime in :)

All right Bane, I've got one for you. I think I figured out a synthesis that would work, but I know there has to be an easier/quicker way. Let's see how this goes over the internet, haha.

Starting material(s): 1-hexene
Product(s): 2-heptanol

So, my thought process for this problem...we end with a carbon chain which is 1 longer than the starting material. So, we need to add a carbon some how. It doesn't seem to me that a nitrile will work. So, I'm thinking we turn the starting material into a grignard and add it to acyl chloride.

Now my problem is getting a bromine on the end of the 1-hexene, which is where I take the round about way of getting there.

I first reacted 1-hexene with Br2 and H20, giving me a secondary alcohol. Now I have a bromine on the end, which I know how to turn into a grignard. I dehydrate the alcohol by adding H+ and heat, leaving me with 1-bromo-2-hexene. I synthesize my grignard by reacting that with Mg and diethylether. I then react that with H2 and Platinum to get rid of the double bond.

Pretty smooth sailing from here. I turn my acetic acid into acyl chloride by reacting it with SOCl2. React the two together, followed by some H+ and I believe I arrive at the correct product, 2-heptanol.

Let me know what you think

[mobikwa]

Bane agreed to help me with some O-chem problems I've been having. That was in a thread in the review section, so I moved it to the misc. Anyone else with o-chem problems or solutions, please chime in :)

All right Bane, I've got one for you. I think I figured out a synthesis that would work, but I know there has to be an easier/quicker way. Let's see how this goes over the internet, haha.

Starting material(s): 1-hexene
Product(s): 2-heptanol

So, my thought process for this problem...we end with a carbon chain which is 1 longer than the starting material. So, we need to add a carbon some how. It doesn't seem to me that a nitrile will work. So, I'm thinking we turn the starting material into a grignard and add it to acyl chloride.

Now my problem is getting a bromine on the end of the 1-hexene, which is where I take the round about way of getting there.

I first reacted 1-hexene with Br2 and H20, giving me a secondary alcohol. Now I have a bromine on the end, which I know how to turn into a grignard. I dehydrate the alcohol by adding H+ and heat, leaving me with 1-bromo-2-hexene. I synthesize my grignard by reacting that with Mg and diethylether. I then react that with H2 and Platinum to get rid of the double bond.

Pretty smooth sailing from here. I turn my acetic acid into acyl chloride by reacting it with SOCl2. React the two together, followed by some H+ and I believe I arrive at the correct product, 2-heptanol.

Let me know what you think

And that's why I'm a mechanical engineer. I have no idea what you said but I give you mad props for saying it...

[Vitruvian]

Reps to Bane whenever he pops in here. That's awesome that he has offered his assistance.

[Beejis60]

That's balls steppy. Is this for first or second semester Ochem?
And I would avoid making the vinyl grignard.

[Kernkraft]

orgo lab was my favorite part of chem other than the math... but I changed to business. Sorry fella. I remember doing reactions like you're talking about but I would have to dust off literally a mound of yellow pads and reread everything to understand.

I would also ask Beejis if I were you to stop in here - he's getting his PhD in organic chemistry.

^^^EDIT - I spoke too late :D

[UWBodybuilding]

And that's why I'm a mechanical engineer. I have no idea what you said but I give you mad props for saying it...

Lol, thanks bro. It's not as awful as everyone says it is. I'm a science man, so it's kind of fun :D


Reps to Bane whenever he pops in here. That's awesome that he has offered his assistance.

For sure. I'm stoked that he wants to help.


That's balls steppy. Is this for first or second semester Ochem?
And I would avoid making the vinyl grignard.

I only have to take 1 semester for my major, so it covers everything, but in less depth. Why would you avoid making the grignard?


orgo lab was my favorite part of chem other than the math... but I changed to business. Sorry fella. I remember doing reactions like you're talking about but I would have to dust off literally a mound of yellow pads and reread everything to understand.

I would also ask Beejis if I were you to stop in here - he's getting his PhD in organic chemistry.

^^^EDIT - I spoke too late :D

Wow, PhD in organic chem is nuts! That's when you can really tell someone is a psycho :p

[Black_Label]

Wow. looking at that im screwed in the spring =)

[Beejis60]

So, my thought process for this problem...we end with a carbon chain which is 1 longer than the starting material. So, we need to add a carbon some how. It doesn't seem to me that a nitrile will work. So, I'm thinking we turn the starting material into a grignard and add it to acyl chloride.

Now my problem is getting a bromine on the end of the 1-hexene, which is where I take the round about way of getting there.

I first reacted 1-hexene with Br2 and H20, giving me a secondary alcohol. Now I have a bromine on the end, which I know how to turn into a grignard. I dehydrate the alcohol by adding H+ and heat, leaving me with 1-bromo-2-hexene. I synthesize my grignard by reacting that with Mg and diethylether. I then react that with H2 and Platinum to get rid of the double bond.


I only have to take 1 semester for my major, so it covers everything, but in less depth. Why would you avoid making the grignard?

Sorry, had to go feast. Anyway, I totally missed your discussion but will cover it in depth now. First of all, you have the 1-bromo-2-ene in a latter step; if you make that into a grignard you will have an allylic grignard (whereas I earlier said vinylic grignard) and the allylic resonance will subsequently get loss of a localized gringnard Mg salt and you will get mixtures of regioisomeric products which is obviously not what you want.
Secondly, your dehydration will give you mixtures of regioisomers of the 1-ene and 2-ene in real life; likely a 50% mix due to the bromonium formation being racemic in the previous few steps. Also when I said it was steppy, I meant that you start with an olefin, then get a 1,2-disubstituted product, you then reform an olefin, and then hydrogenate it.... Sounds very counter-productive no?
Have you guys covered oxidations? What about borane reductions?

[UWBodybuilding]

No problem, man. I'm just happy to have help :)

If I was going to make a grignard I'd have to do it in a different order so I only get the one I want, so I did mess up there.

And the reason I added Br2/H2O as the first step is because that's the only way I know how to get the bromine on the terminal carbon. If I reacted the alkene with HBr I'd get the bromine on the second carbon instead, which wouldn't be the correct grignard I was looking for in the end.

I see what you mean about the dehydration yielding 2 different products, but I don't think we covered it in that depth. We just assume that the most stable molecule forms primarily and go from there. Like I said, covering lots of material, but in less depth.

Looking back through my notes I think I've come up with a much better synthesis. This time I reacted the starting alkene with 1)BH3 and 2)H2O2/NaOH leading to hexanol. Then oxidize that to the aldehyde with PCC and CH2Cl2. Finally, I added a much simpler grignard, CH3MgBr, then H+/H2O to protonate to the secondary alcohol.

Look better?

[UWBodybuilding]

Wow. looking at that im screwed in the spring =)

Nah brah. It looks more complicated all in text like that. A lot easier writing it on paper :)

[Beejis60]

Look better?

That's exactly what I have.

[UWBodybuilding]

That's exactly what I have.

:D :D :D

Maybe I am getting the hang of this o-chem business!

So, PhD in o-chem...do you plan on being a professor then?

[Beejis60]

So, PhD in o-chem...do you plan on being a professor then?

I would like to.

[UWBodybuilding]

I would like to.

Very respectable. Good luck, man.

Thanks for the help! :D

[Patrick Arnold]

Bane agreed to help me with some O-chem problems I've been having. That was in a thread in the review section, so I moved it to the misc. Anyone else with o-chem problems or solutions, please chime in :)

All right Bane, I've got one for you. I think I figured out a synthesis that would work, but I know there has to be an easier/quicker way. Let's see how this goes over the internet, haha.

Starting material(s): 1-hexene
Product(s): 2-heptanol

So, my thought process for this problem...we end with a carbon chain which is 1 longer than the starting material. So, we need to add a carbon some how. It doesn't seem to me that a nitrile will work. So, I'm thinking we turn the starting material into a grignard and add it to acyl chloride.

Now my problem is getting a bromine on the end of the 1-hexene, which is where I take the round about way of getting there.

I first reacted 1-hexene with Br2 and H20, giving me a secondary alcohol. Now I have a bromine on the end, which I know how to turn into a grignard. I dehydrate the alcohol by adding H+ and heat, leaving me with 1-bromo-2-hexene. I synthesize my grignard by reacting that with Mg and diethylether. I then react that with H2 and Platinum to get rid of the double bond.

Pretty smooth sailing from here. I turn my acetic acid into acyl chloride by reacting it with SOCl2. React the two together, followed by some H+ and I believe I arrive at the correct product, 2-heptanol.

Let me know what you think

how about making the double bond into an epoxide? than methyl grignard. just a thought

[_NimbusTim_]

how about making the double bond into an epoxide? than methyl grignard. just a thought

What would you know!

:eek:

[40-Yard Dash_2]

What would you know!

:eek:

He is to chemistry what you are to guy-on-guy porn.

[_NimbusTim_]

He is to chemistry what you are to guy-on-guy porn.

I'm :confused: .....am I guy 1 and your guy 2, or vice versa?

[Beejis60]

how about making the double bond into an epoxide? than methyl grignard. just a thought

You will get the 3-ol, noob.

[Kernkraft]

You will get the 3-ol, noob.

lol!

[UWBodybuilding]

You will get the 3-ol, noob.

Yeah, noob.

[Black_Label]

Nah brah. It looks more complicated all in text like that. A lot easier writing it on paper :)

Someone told me it was all memorizing, maybe that was the Bio. I dont know anymore, I am just getting it done.

[michael3435]

jesus this thread is a great idea with bane, patrick, and beejis here. wish i had this opportunity, i had to take orgo twice lol...although the first time i shoulda passed.

[Patrick Arnold]

ok. you need to do anti-markovnikoff addition to the alkene. hydroboration followed by oxidation and hydrolysis

that will give you the aldehyde

then methyl grignard will give you the 2 substituted alcohol

[Patrick Arnold]

You will get the 3-ol, noob.

i am gonna oxidize your face

[UWBodybuilding]

Looking back through my notes I think I've come up with a much better synthesis. This time I reacted the starting alkene with 1)BH3 and 2)H2O2/NaOH leading to hexanol. Then oxidize that to the aldehyde with PCC and CH2Cl2. Finally, I added a much simpler grignard, CH3MgBr, then H+/H2O to protonate to the secondary alcohol.

Look better?


ok. you need to do anti-markovnikoff addition to the alkene. hydroboration followed by oxidation and hydrolysis

that will give you the aldehyde

then methyl grignard will give you the 2 substituted alcohol

^^^ Look good?


Someone told me it was all memorizing, maybe that was the Bio. I dont know anymore, I am just getting it done.

There is a certain amount of memorizing, but there is also a deeper reason why these reactions take place. If you can understand the deeper reasons it's much easier to predict products.


jesus this thread is a great idea with bane, patrick, and beejis here. wish i had this opportunity, i had to take orgo twice lol...although the first time i shoulda passed.

Lol, what happened the first time?

[Patrick Arnold]

^^^ Look good?



i didnt see that. yeah you got it

anymore problems?

[UHCougar05]

jesus this thread is a great idea with bane, patrick, and beejis here. wish i had this opportunity, i had to take orgo twice lol...although the first time i shoulda passed.I was a ChemE and took orgo I: I ended up with a 27 for the semester, which was a D. I said to myself, "Maybe I'm not ChemE material...", then I changed majors.

[_J-BONE_]

I was a ChemE and took orgo I: I ended up with a 27 for the semester, which was a D. I said to myself, "Maybe I'm not ChemE material...", then I changed majors.

I almost failed high school Chemistry...that's when I decided business was my desired path...lol

[bloodsimple1234]

PA tutors too!

[michael3435]

^^^ Look good?



There is a certain amount of memorizing, but there is also a deeper reason why these reactions take place. If you can understand the deeper reasons it's much easier to predict products.



Lol, what happened the first time?

i got really sick during 2 out of 3 of the tests...bad luck i guess. the one i took i got an 11 lol. didnt really have a chance.


I was a ChemE and took orgo I: I ended up with a 27 for the semester, which was a D. I said to myself, "Maybe I'm not ChemE material...", then I changed majors.

haha, its a shame because i actually like the material. its just that some departments take things way too seriously

[UHCougar05]

I almost failed high school Chemistry...that's when I decided business was my desired path...lolYeah, I hear ya. I graduated with my BS in Econ and I'm going back next summer to take some accounting courses so that I can sit for the CPA some time in 2011.

[Beejis60]

i am gonna oxidize your face

lol, I'll shoot a half-reacted Swern in your face... that will smell delicious.

[bloodsimple1234]

i got really sick during 2 out of 3 of the tests...bad luck i guess. the one i took i got an 11 lol. didnt really have a chance.



haha, its a shame because i actually like the material. its just that some departments take things way too seriously

you aren't kidding,goes for a lot of schools.Some departments/professors are actually out to get students.Im convinced of it!

[Patrick Arnold]

lol, I'll shoot a half-reacted Swern in your face... that will smell delicious.


would you like your next csc bottle to be pyridine or butyric acid flavor? tell me now

[MJ1331]

would you like your next csc bottle to be pyridine or butyric acid flavor? tell me now

last summer i spent ~200 hours doing pyridine hemochrome assays in a room with a broken hood just so i could publish a paper before school started. It was aweful.

[UWBodybuilding]

i didnt see that. yeah you got it

anymore problems?

Perhaps. I'm just having a problem seeing the steps. I know the reactions, but when you get a bigger molecule it makes things look more complicated than it really is. I'm going to study more tonight and I'll post problems :)


would you like your next csc bottle to be pyridine or butyric acid flavor? tell me now

I'll take some isobutyl formate please!

[Beejis60]

would you like your next csc bottle to be pyridine or butyric acid flavor? tell me now

ummm, yes.


So basically stinky fish or vomit flavored? I'd go with stinky fish, sounds healthier.

Nah man, pyridine smells more like rotten milk IMO; I actually call triethylamine stinky fish pussy unless women or profs are around.


last summer i spent ~200 hours doing pyridine hemochrome assays in a room with a broken hood just so i could publish a paper before school started. It was aweful.

you poor poor bastard; you know the smell is worse for you than getting that shyt on you right? If you spent near 200 hrs in three months breathing in that shyt, you're probably sterile by now (srs).

[MJ1331]

ummm, yes.



Nah man, pyridine smells more like rotten milk IMO; I actually call triethylamine stinky fish pussy unless women or profs are around.



you poor poor bastard; you know the smell is worse for you than getting that shyt on you right? If you spent near 200 hrs in three months breathing in that shyt, you're probably sterile by now (srs).

That was the worst smelling thing i have ever smelled. To get specific the hood was only broken for about 1 week so hopefully that doesn't have any long term affects. I checked the MSDS and talked to few professors to ensure i would encounter any problems. They were more concerned about me passing out. If i remember correctly, the infertility is largely attributed to skin exposure. but then again, ill tell you in a few years if it affected the boys

[Beejis60]

That was the worst smelling thing i have ever smelled.

I was quenching a bunch of decomposed Dess-Martin reagent one time and it stunk up my whole lab like dimethyl sulfide. I then decided to add bleach and it stunk like pet ether + something equally shytty as dimethyl sulfide. Was the worst day or two AND all of the quenching was done in my hood with the sash mostly down.


They were more concerned about me passing out.

from what? were you working with ether or toluene? Those are the only times I got pretty high and have come close to feeling dizzy and passing out.


If i remember correctly, the infertility is largely attributed to skin exposure. but then again, ill tell you in a few years if it affected the boys

Naw, that's a myth; it can and is often attributed to skin exposure but inhalation is the worst. Can't remember where I discovered that...

[UWBodybuilding]

Well, here is the morning of the second biggest o-chem day of my life. I have my 3rd and final midterm at 11:00 midwest time. Then on the 21st I have my final. Let's do this!

Thanks for the help so far guys :)

[MJ1331]

Well, here is the morning of the second biggest o-chem day of my life. I have my 3rd and final midterm at 11:00 midwest time. Then on the 21st I have my final. Let's do this!

Thanks for the help so far guys :)

good luck!

[Beejis60]

Well, here is the morning of the second biggest o-chem day of my life. I have my 3rd and final midterm at 11:00 midwest time. Then on the 21st I have my final. Let's do this!

:confused: there's no such thing as midwest time :confused:

[UWBodybuilding]

:confused: there's no such thing as midwest time :confused:

Lulz, my bad. Central time. I only got 4hrs of sleep last night :(

But, the exam went extremely well! I couldn't believe it. Like I said before, I know the individual reactions, but it's hard for me to see the big picture when it comes to more complex molecules. But it all came together for some reason during the exam! LOL

I'm not complaining :D I'll find out later today what I got.

[40-Yard Dash_2]

Lulz, my bad. Central time. I only got 4hrs of sleep last night :(

But, the exam went extremely well! I couldn't believe it. Like I said before, I know the individual reactions, but it's hard for me to see the big picture when it comes to more complex molecules. But it all came together for some reason during the exam! LOL

I'm not complaining :D I'll find out later today what I got.

Hope you didn't fail. Every time I thought I did halfway decent or better than expected, I usually made a lot worse than I imagined. Of course when I felt I bombed it, I bombed it.

The only times I did really well when I knew for a fact I aced it, because there was no doubt.

[Beejis60]

Hope you didn't fail. Every time I thought I did halfway decent or better than expected, I usually made a lot worse than I imagined. Of course when I felt I bombed it, I bombed it.

The only times I did really well when I knew for a fact I aced it, because there was no doubt.

Everytime I thought I raped a test, I did.

[neuron]

i want to see bane answer the next one

[adrenergic]

I love carbon.

[rushki]

subscribing to this hur thread and using the genius it comes with in one month when it is my turn to battle ochem

[chasinSKURT]

Hope you didn't fail. Every time I thought I did halfway decent or better than expected, I usually made a lot worse than I imagined. Of course when I felt I bombed it, I bombed it.

The only times I did really well when I knew for a fact I aced it, because there was no doubt.

Used to hate getting back a chem exam. Even if I had the right idea, I'd fawk up a significant figure. Our professors were anal as hell about little shyt like that.

[Beejis60]

Used to hate getting back a chem exam. Even if I had the right idea, I'd fawk up a significant figure. Our professors were anal as hell about little shyt like that.

Ever take analytical and/or quantitative analysis? Class freaking BLEW ass; you thought you knew sig figs then you get -10 for wrong sigfigs..... FAAAWWWKKK!!!

Sorry, flashbacks to undergrad days :mad:

[UWBodybuilding]

Average for this exam: 69.5%

My score: 81.5$

My first 'A' on an O-chem test (last 2 were B's)!!!

I'll start studying for the final soon, so I'll be needing some help. Thanks for everyone who's participated in this thread so far!

[Redcutter]

I hope this thread is still around for me next fall lol